CN101870765B - 9-芳基和双芳基取代的聚芴 - Google Patents
9-芳基和双芳基取代的聚芴 Download PDFInfo
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- CN101870765B CN101870765B CN201010213318.XA CN201010213318A CN101870765B CN 101870765 B CN101870765 B CN 101870765B CN 201010213318 A CN201010213318 A CN 201010213318A CN 101870765 B CN101870765 B CN 101870765B
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- 229920002098 polyfluorene Polymers 0.000 title description 7
- 229920000642 polymer Polymers 0.000 claims abstract description 73
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
- 239000000178 monomer Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 22
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 125000005620 boronic acid group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 7
- 125000005259 triarylamine group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002800 charge carrier Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 230000003381 solubilizing effect Effects 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical class C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 3
- 150000002390 heteroarenes Chemical class 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 125000005621 boronate group Chemical group 0.000 claims description 2
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- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 abstract description 4
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 10
- 238000004770 highest occupied molecular orbital Methods 0.000 description 6
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- 229920001519 homopolymer Polymers 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
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- -1 nitro, carboxyl Chemical group 0.000 description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 4
- 230000027756 respiratory electron transport chain Effects 0.000 description 4
- 241001120493 Arene Species 0.000 description 3
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- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical class C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
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- PZWLRLIAVLSBQU-UHFFFAOYSA-N 1,2-dioctyl-9h-fluorene Chemical group C1=CC=C2C3=CC=C(CCCCCCCC)C(CCCCCCCC)=C3CC2=C1 PZWLRLIAVLSBQU-UHFFFAOYSA-N 0.000 description 1
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
- IJVBYWCDGKXHKK-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetraphenylbenzene-1,2-diamine Chemical class C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IJVBYWCDGKXHKK-UHFFFAOYSA-N 0.000 description 1
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- BYDIWLYAWBNCAQ-UHFFFAOYSA-N 9,9-bis(4-methoxyphenyl)fluorene Chemical compound C1=CC(OC)=CC=C1C1(C=2C=CC(OC)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BYDIWLYAWBNCAQ-UHFFFAOYSA-N 0.000 description 1
- RXACYPFGPNTUNV-UHFFFAOYSA-N 9,9-dioctylfluorene Chemical compound C1=CC=C2C(CCCCCCCC)(CCCCCCCC)C3=CC=CC=C3C2=C1 RXACYPFGPNTUNV-UHFFFAOYSA-N 0.000 description 1
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical group C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 238000004608 ZINDO calculation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- TVZISJTYELEYPI-UHFFFAOYSA-N hypodiphosphoric acid Chemical compound OP(O)(=O)P(O)(O)=O TVZISJTYELEYPI-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- APCOQCLKCAFINS-UHFFFAOYSA-N n,n-bis(4-bromophenyl)-4-butan-2-ylaniline Chemical compound C1=CC(C(C)CC)=CC=C1N(C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 APCOQCLKCAFINS-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08G2261/14—Side-groups
- C08G2261/146—Side-chains containing halogens
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08G2261/14—Side-groups
- C08G2261/148—Side-chains having aromatic units
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/149—Side-chains having heteroaromatic units
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- C—CHEMISTRY; METALLURGY
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/51—Charge transport
- C08G2261/514—Electron transport
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- C—CHEMISTRY; METALLURGY
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/50—Physical properties
- C08G2261/52—Luminescence
- C08G2261/522—Luminescence fluorescent
- C08G2261/5222—Luminescence fluorescent electrofluorescent
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1433—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Physics & Mathematics (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0225869.7 | 2002-11-06 | ||
| GBGB0225869.7A GB0225869D0 (en) | 2002-11-06 | 2002-11-06 | Polymer |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2003801057632A Division CN1726243A (zh) | 2002-11-06 | 2003-11-04 | 9－芳基和双芳基取代的聚芴 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101870765A CN101870765A (zh) | 2010-10-27 |
| CN101870765B true CN101870765B (zh) | 2015-06-24 |
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| DE112005003032T5 (de) * | 2004-12-03 | 2007-12-13 | Sumitomo Chemical Co., Ltd. | Salicylat-substituierte konjugierte Polymere und Vorrichtungen |
| KR101249640B1 (ko) * | 2004-12-06 | 2013-04-01 | 에스케이이노베이션 주식회사 | 9-플루오렌-2-일-9-아릴-2,7-플루오레닐 단위 함유전기발광고분자 및 이를 이용한 전기발광소자 |
| WO2006062323A1 (en) * | 2004-12-06 | 2006-06-15 | Sk Corporation | Electroluminescent polymer having 9-fluoren-2-yl-9-aryl-2,7-fluorenyl unit and electroluminescent device manufactured using the same |
| GB2440934B (en) | 2006-04-28 | 2009-12-16 | Cdt Oxford Ltd | Opto-electrical polymers and devices |
| US20090302748A1 (en) | 2006-08-01 | 2009-12-10 | Sumitomo Chemical Company, Limited | Polymer compound and polymer light emitting device |
| KR20090053949A (ko) * | 2006-09-13 | 2009-05-28 | 스미또모 가가꾸 가부시키가이샤 | 고분자 화합물 및 고분자 발광 소자 |
| JP5762745B2 (ja) * | 2007-10-24 | 2015-08-12 | メルク パテント ゲーエムベーハー | 光電子デバイス |
| GB2454890B (en) * | 2007-11-21 | 2010-08-25 | Limited Cambridge Display Technology | Light-emitting device and materials therefor |
| CN101591219B (zh) * | 2008-05-29 | 2012-08-08 | 中国科学院化学研究所 | 一种功能化聚芴类化合物及其中间体与应用 |
| DE102008045663A1 (de) * | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Fluorverbrückte Assoziate für optoelektronische Anwendungen |
| DE102009034194A1 (de) * | 2009-07-22 | 2011-01-27 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
| US20110077373A1 (en) * | 2009-09-29 | 2011-03-31 | General Electric Company | Polymer and optoelectronic device comprising the same |
| TWI401274B (zh) * | 2009-10-16 | 2013-07-11 | Univ Nat Taiwan Science Tech | 新穎高分子聚合物及共聚合物及其製備方法 |
| KR101663185B1 (ko) * | 2009-11-20 | 2016-10-06 | 삼성전자주식회사 | 플루오로기-함유 고분자, 상기 고분자를 포함한 유기 발광 소자 및 상기 유기 발광 소자의 제조 방법 |
| JP5710993B2 (ja) * | 2010-01-28 | 2015-04-30 | 住友化学株式会社 | 高分子化合物及びそれを用いてなる発光素子 |
| EP2530100B1 (en) * | 2010-01-28 | 2015-10-21 | Sumitomo Chemical Co., Ltd | Polymer compound and light-emitting device using same |
| DE102010033080A1 (de) * | 2010-08-02 | 2012-02-02 | Merck Patent Gmbh | Polymere mit Struktureinheiten, die Elektronen-Transport-Eigenschaften aufweisen |
| JP5750247B2 (ja) * | 2010-08-31 | 2015-07-15 | 住友化学株式会社 | 有機薄膜トランジスタ及びその製造方法 |
| GB2483269A (en) * | 2010-09-02 | 2012-03-07 | Cambridge Display Tech Ltd | Organic Electroluminescent Device containing Fluorinated Compounds |
| JP5883570B2 (ja) * | 2011-03-25 | 2016-03-15 | 国立大学法人横浜国立大学 | 積層構造体 |
| US20140246400A1 (en) * | 2011-09-30 | 2014-09-04 | Mitsubishi Gas Chemical Company, Inc. | Resin having fluorene structure and material for forming underlayer film for lithography |
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- 2003-11-04 EP EP10184752A patent/EP2363423A1/en not_active Withdrawn
- 2003-11-04 CN CN201010213318.XA patent/CN101870765B/zh not_active Expired - Fee Related
- 2003-11-04 AU AU2003285484A patent/AU2003285484A1/en not_active Abandoned
- 2003-11-04 EP EP03778486A patent/EP1569980B1/en not_active Expired - Lifetime
- 2003-11-04 CN CN200910140587A patent/CN101696220A/zh active Pending
- 2003-11-04 KR KR1020057008051A patent/KR100604500B1/ko not_active Expired - Fee Related
- 2003-11-04 WO PCT/GB2003/004753 patent/WO2004041902A2/en not_active Ceased
- 2003-11-04 JP JP2004549336A patent/JP4293991B2/ja not_active Expired - Lifetime
- 2003-11-04 AT AT03778486T patent/ATE554121T1/de active
- 2003-11-04 US US10/533,989 patent/US7494720B2/en not_active Expired - Lifetime
- 2003-11-04 CN CNA2003801057632A patent/CN1726243A/zh active Pending
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- 2008-10-27 JP JP2008275027A patent/JP5283479B2/ja not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| KR100604500B1 (ko) | 2006-07-25 |
| AU2003285484A1 (en) | 2004-06-07 |
| ATE554121T1 (de) | 2012-05-15 |
| CN101696220A (zh) | 2010-04-21 |
| KR20060011819A (ko) | 2006-02-03 |
| WO2004041902A3 (en) | 2004-08-12 |
| JP2006505647A (ja) | 2006-02-16 |
| JP4293991B2 (ja) | 2009-07-08 |
| WO2004041902A2 (en) | 2004-05-21 |
| JP2009097016A (ja) | 2009-05-07 |
| CN1726243A (zh) | 2006-01-25 |
| AU2003285484A8 (en) | 2004-06-07 |
| US7494720B2 (en) | 2009-02-24 |
| GB0225869D0 (en) | 2002-12-11 |
| EP1569980B1 (en) | 2012-04-18 |
| EP2363423A1 (en) | 2011-09-07 |
| CN101870765A (zh) | 2010-10-27 |
| EP1569980A2 (en) | 2005-09-07 |
| US20060228576A1 (en) | 2006-10-12 |
| JP5283479B2 (ja) | 2013-09-04 |
| US20090167170A1 (en) | 2009-07-02 |
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